Verse Round Up
Canon
All events that happened within the Star Trek XI up to the point the USS Enterprise crew is officially assigned to the ship happen within this area.
Hilltop Mansions
Leonard McCoy, like many other boys, went straight to the recruiters office as soon as he graduated high school and signed up for a hitch in the Army. His long time girlfriend supported his decision to go off to war and promised to wait for him while he served their country but six months later she sent a 'Dear John' letter. When Len's tour ended, Len signed up for another four years and didn't look back. He tried to forget all about his girl, all about the hopes and dreams of coming home, getting married, and maybe starting a family.
When Leonard finally came home, this time for good, he didn't return to Georgia, instead moving from town to town, drifting from odd job to odd job until he met Christopher Pike. Now Leonard works for Fleet Security as a bodyguard to the elite and somehow got himself contracted out to guard a pampered rocker named Jim Kirk. Somehow, this is a hell of a lot more harrowing than the war was.
The Road Less Traveled
Jocelyn's lawyers were vicious and cruel, much like the woman who hired them, but Leonard's were smart and outmaneuvered the circling sharks. He lost the cars, the art, and, unfortunately, his job but kept the house and custody of his young daughter. He had to pull himself together, cut down on the drinking and pull himself out of the depressive spiral he'd been in since his father died because he had a little girl counting on him. The offer from Starfleet came shortly after. Leonard signed himself up and sold his house, putting the money in savings account for Joanna, and packed them both off to living in family housing on base.
Never Happened
So what would happen if Spock had made it in time to Romulan to stop the supernova? There were no rogue Romulans seeking revenge on the Federation, the Kelvin completed its mission unmolested, and James T. Kirk was born, still premature, but to two parents, not just one. Life went on, time moved forward, and Leonard McCoy never enlisted. The world's relatively as safe as it always is and, presumably, always will be.
But without Starfleet, what does Leonard have? Well, he's still divorced but he's still got his job at the hospital. Life's good. Normal. Or is it? What happens when people that he would have met, should have met, start trickling into his life? Pike, Kirk, even Sulu and Chekov make appearances. How or why, well that remains to be seen.
Hard Knock Life: An offshoot of HM wherein Kirk and several members of the band have been injured due to an accident during a show. It was purely preventable, or so says Leonard who had warned of the unsafe conditions but was ultimately ignored, and now Jim is banged up and the band is unable to continue the tour. Leonard's now watching over Kirk's safety in a house Jim bought and set up in the Catskills.